Hydrochloric Acid → N-benzyloxy-2-ethoxy-3-[4-(2-{4-methanesulfonyloxy-phenyl}ethoxy)phenyl]propanoic amide

HRID 987230Notes

Reaction equation

HRID 987230 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[OH:16][N:17]1C(=O)CCC1=O.[CH2:24]([O:26][CH:27]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][S:48]([CH3:51])(=[O:50])=[O:49])=[CH:43][CH:42]=2)=[CH:34][CH:33]=1)[C:28]([OH:30])=O)[CH3:25].C(N(C(C)C)CC)(C)C.[CH2:61](NO)[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1.Cl>C(#N)C.CCCCCCC>[CH2:61]([O:16][NH:17][C:28](=[O:30])[CH:27]([O:26][CH2:24][CH3:25])[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([O:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][S:48]([CH3:51])(=[O:49])=[O:50])=[CH:43][CH:42]=2)=[CH:36][CH:37]=1)[C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 81531DiisopropylethylamineHCID 2794173BenzylhydroxylamineHCID 113387772-Ethoxy-3-[4-(2-{4-[(methanesulfonyl)oxy]phenyl}ethoxy)phenyl]propanoic acid

Product 1

HCID 22988722N-benzyloxy-2-ethoxy-3-[4-(2-{4-methanesulfonyloxy-phenyl}ethoxy)phenyl]propanoic amideYield 66%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8900HeptaneSolvent

Procedure

DCC (1 g; 4.85 mmole) and N-hydroxy-succinimide acid (0.56 g; 4.85 mmole) were added to a solution of 2-ethoxy-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl]propanoic acid (described in Example 2) (1.65 g; 4.04 mmole) in acetonitrile (25 ml) at 0° C. After 1 hour a precipitate was filtered off and diisopropylethylamine (1.82 g; 14.1 mmole) and benzyl hydroxylamine (1.24 g; 8.08 mmole) dissolved in acetonitrile were added. After stirring overnight hydrochloric acid (2M) was added and the mixture was extracted with diethyl ether. The organic phase was washed with sodium carbonate solution and dried (magnesium sulfate). The solvent was removed and the crude product was purified by chromatography on silica gel using ethyl acetate:heptane (gradient 10-100% ethyl acetate) as eluant to give 1.36 g (yield 66%) of N-benzyloxy-2-ethoxy-3-[4-(2-{4-methanesulfonyloxy-phenyl}ethoxy)phenyl]propanoic amide.

Workup

  1. filtrationAfter 1 hour a precipitate was filtered off
  2. additionwere added
  3. additionwas added
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe organic phase was washed with sodium carbonate solution
  6. dry with materialdried (magnesium sulfate)
  7. customThe solvent was removed
  8. customthe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b75c8260ed934ba1bc63e58b2a917004
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

Loading…